Pyridine → HCID 46181225, compound

HRID 2380977Notes

Reaction equation

HRID 2380977 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]1[CH:33]=[C:32]([S:34](Cl)(=[O:36])=[O:35])[N:31]=[CH:30]1.N1C=CC=CC=1>ClCCl>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[S:34]([C:32]1[N:31]=[CH:30][N:29]([CH3:28])[CH:33]=1)(=[O:36])=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 67134440HCID 67134440, compound

Product 1

HCID 46181225HCID 46181225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl-[4-(4-phenyl-piperazin-1-yl methyl)-phenyl)-amine (30 mg, 0.08 mmol), 1-methylimidazole-4-sulfonyl chloride (51 mg, 0.27 mmol) and pyridine (24 μl, 0.30 mmol) in dry dichloromethane (2 ml) were heated to reflux for 15 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was purified by column chromatography (5% methanol in dichloromethane) to afford the title compound as an off white solid (22 mg, 55%). HPLC retention time 7.04 min. Mass spectrum (ES+) m/z 502 (M+H). 1H-NMR (CDCl3) δH 2.54 (4H, m, 2×CH2), 3.16 (4H, m, 2×CH2), 3.45 (2H, br s, CH2), 3.71 (3H, s, CH3), 4.99 (2H, s, CH2), 6.84 (1H, t, J=7.3 Hz, ArH), 6.89 (2H, m, 2×ArH), 7.10 (2H, m, 2×ArH), 7.17-7.30 (10H, m, 10×ArH), 7.55 (1H, m, ArH).

Workup

  1. temperatureto reflux for 15 h
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified by column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1f4705bdc8134895b0ea52cf01b9fac1
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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